Water → 8-Benzyl-7,8-dihydro-5-methyl-6H-pyrazolo[1,5-a]pyrrolo-[3,2-e]pyrimidine

HRID 345093Notes

Reaction equation

HRID 345093 reaction equation
Cl[C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([CH3:11])[C:3]=1[CH2:12][CH2:13]Cl.[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C.O>C(O)(C)C>[CH2:15]([N:22]1[C:2]2[N:7]3[N:8]=[CH:9][CH:10]=[C:6]3[N:5]=[C:4]([CH3:11])[C:3]=2[CH2:12][CH2:13]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7504BenzylamineHCID 8471TriethylamineHCID 156758537-Chloro-6-(2-chloroethyl)-5-methylpyrazolo[1,5-a]pyrimidine

Product 1

HCID 156757968-Benzyl-7,8-dihydro-5-methyl-6H-pyrazolo[1,5-a]pyrrolo-[3,2-e]pyrimidineYield 60%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 1.15 g (5 mmoles) of 7-chloro-6-(2-chloroethyl)-5-methylpyrazolo[1,5-a]pyrimidine (prepared as described in Example 3), 643 mg (6 mmoles) of benzylamine and 2 ml of triethylamine dissolved in 5 ml of isopropanol was heated under reflux for 7 hours, with stirring. The reaction mixture was then poured into water and extracted with ethyl acetate. The organic layer was extracted with 5% by volume aqueous sulfuric acid, and the extract was made basic by the addition of sodium carbonate. The crystals which precipitated were collected by filtration and washed with water. They were then purified by column chromatography through silica gel (eluted with chloroform) and recrystallized from a mixture of ethyl acetate and chloroform, to afford 788 mg (yield 60%) of the title compound as colorless needles, melting at 130°-130.5° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 7 hours
  3. extractionextracted with ethyl acetate
  4. extractionThe organic layer was extracted with 5% by volume aqueous sulfuric acid
  5. additionthe extract was made basic by the addition of sodium carbonate
  6. customThe crystals which precipitated
  7. filtrationwere collected by filtration
  8. washwashed with water
  9. customThey were then purified by column chromatography through silica gel (eluted with chloroform)
  10. customrecrystallized from a mixture of ethyl acetate and chloroform

Sources & evidence

ORD record
ord-f19d33bed97541c7919e3d8a0d7d732c
Source dataset
uspto-grants-1991_10
Patent number
US05055479

Reaction notes

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